Genres: BDSM, Bondage, Humilation, Torture, Toys, Domination, Big Tits, Squirt
She is struggling to remain free but the way the rope around her neck connects to the pulley, there is no way Penny Barber can resist the pulling her into her new box. She hates feeling claustrophobic. Between the cage and the hood she knows this is going to be terrifying. She has tears running down her face before she is even locked in. It wouldn't be so bad if she could manipulate the bondage herself but the way her hands are wrapped up she can't get a grip that would allow her any kind of relief. The key is to make being outside of the box much more frightening than being inside. To do this OT employs some serious corporal punishment. Chains keep her bound between two posts while he works his whip across her ass and the backs of her thighs. Flipping it between her legs he lands several sharp blows right across her clit and pussy lips. Even the orgasms are meant to be painful. The pogo between her legs doesn't let her relax at all. As the vibrator makes her weak in the knees and her body begins to slide down the shaft she feels the pressure pushing it further inside of her. There is a bruise forming on her leg from the paddling she is enduring, all the while trying to focus on the feeling between her legs. She wants to cum. The longer she fights it the harder it will be to stay on her feet. How many times can she cum in one day? How much pain can she endure between orgasms? Every time OT rebinds her Penny knows something worse is coming. Every position has its own trials and vulnerabilities. Each one leaves her open to assault from another angle. The punishments, vibrators, and orgasms all get more intense with each new bind.
Some adventures are just so much fun and so iconic that they beg for a sequel. I feel the call of the Golden Gate Bridge on every rare sunny day in San Francisco. It is time to tie a sissy to the most famous bridge in the world and see how much we can get away with in my home town!
10,000 people or more will see us today as they drive past our colorful "performance art" scene. Even more will see Sissy Stephanie on the internet once this video is posted on my site. I am training her to be a slutty exhibitionist and this sets a new high water mark of truly public humiliation.
Sissy Stephanie is up to the challenge, so we add a butt plug to make our walk more interesting. Cruel Mistress Vyra also comes with us as an in case our sissy maid tries to run. I'm wearing my favorite rubber Alice in Wonderland dress and we are ready to give the tourists something to talk about. I love how the wind blows our petticoats up, we are all wearing maximum layers of ruffles to take advantage of the gusty weather...
Time for a humiliating holiday threesome with Lady Evadne! I get the feeling this is the start of a very special Easter tradition...
I bind our Easter Bunny's balls with a metal cock ring and special handmade chainmaille "string" to isolate and puff them up so they look like two eggs, ready to be painted. There's a reason why the Spanish word for testicles is huevos!
One side gets cheerful polka dots, the other gets bright neon stripes! I love collaborating with fellow artists like Lady Evadne, but it is even better when we can combine our kinks with our paintbrushes!
Once his balls are properly decorated, we make him to fuck a hollow chocolate rabbit. I bite off the ears, then start gnawing on his cock inside, until the chocolate starts to melt from his body heat...
Give a man an orgasm and he will forget about it in a few days.
Deny a man that same orgasm and he will remember it for the rest of his life.
It is my slave's sixth week in unrelenting chastity. This is a real treat, to be in the Gates of Hell means a lot less pain and room to get almost fully erect. Think of it as a limited opportunity to stretch coupled with sadistic tease and denial! Even while his dick is locked up, there are plenty of erogenous zones available for me to play with.
This is the most gentle chastity device that he has worn in a long time. The spike marks from the Kali's Teeth Bracelet are still clearly visible, a lasting warning not to test my patience. For now, he has gained a reward...
"This is exciting! I hope it looks like a bright pink light sabre in her ass!" Denali is thrilled by the spectacle unfolding at our spring celebration.
Mistress Sofia loves creating increasingly humiliating nicknames for Sissy Joy, starting with Sugar Tits, but now "Bubble Butt" is on the menu. She found a phallic container of bright pink bubbles and she wants to shove it up Joy's sissy hole!!!
This is how you earn a "Deed Name" in Bondageland.
We bend her over an upside down wheelbarrow, anchoring her spread legs and arms firmly, so there is no escape. Poor Joy begs for mercy and even cries in this scene. Despite her struggles, we eventually make the improvised toy all the way in. Joy now officially has a Bubble Butt!!!
The real cruelty comes when our sissy can't hold onto her bubbles long enough for us to blow them. Poor sissy's butt rebels against us and she must be cleaned up. I don't want her tracking a mess into the farmhouse, so we use the garden hose to wash her down...